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Controlling Stereoselectivity in Tribromide Mediated Oxidative Dearomatisations – Synthesis of Selective Spirofurano‐naphthalones
Author(s) -
Sarkar Debayan,
Kuila Puspendu,
Sood Devashish
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900974
Subject(s) - stereoselectivity , chemistry , tribromide , ammonium , oxidative phosphorylation , solvent , organic chemistry , combinatorial chemistry , catalysis , biochemistry
A series of ammonium tribromides were screened for exploring the role of ammonium counterpart attached to tribromides on generation of stereoselective spiro‐furans via oxidative dearomatisation of naphthols. The proposition enlightens a suitable combination of the ammonium tribromide and solvent employed, deliver the best achieved diastereoselectivities. This in turn, has also envisioned the mechanistic aspects related to this category of reactions. The mentioned dearomative spiro‐furano naphthalones has also been successfully achieved on a large‐scale.